Method for controlling parasitic fungi in cultivated plants

ABSTRACT

A method for controlling harmful fungi in crop plants having modified pathogen resistance to certain harmful fungi, where the crop plant is treated with an active compound from the class of the strobilurins.

This appln is a 371 of PCT/EP97/05534 filed Oct. 8, 1997.

The present invention relates to a process for controlling harmful fungiin crop plants having modified pathogen resistance against, for example,other harmful fungi.

Methods for controlling harmful fungi in crop plants by usingfungicidally active compounds are known per se and are disclosed in theliterature.

Also known are crop plants whose pathogen resistance to certain harmfulfungi which have a particularly adverse effect on the respective cropplant is modified or increased as compared to the natural level. Thismay be achieved, for example, by selective breeding or by geneticengineering in that certain DNA sequences which cause increased pathogenresistance when they are functionally expressed in the plant areintroduced into the crop plant.

However, owing to the large number of damage-causing mechanisms ofharmful fungi, it is often only possible to increase the resistance to asmall group of harmful fungi. In addition, plants which are modified inthis way often have other disadvantages, for example a lower harvestyield, a higher susceptibility to other harmful fungi, etc.

It is an object of the present invention to provide a method forcontrolling harmful fungi which allows the control of a wide range ofharmful fungi without adversely affecting the yield characteristics ofthe plants.

We have found that this object is achieved by the method mentioned atthe outset, wherein crop plants having modified pathogen resistance toharmful fungi are treated with an active compound of the formula I (IAor IB).

Active compounds of the formula IA or IB are known per se and referredto in the literature as the class of the “strobilurins”, in someinstances also as “β-methoxyacrylates” (cf. H. Sauter et al.,“Mitochondrail [sic] respiration as a target for antifungals: lessonsfrom research in strobilurins” in “Antifungal agents—Discovery and modeof action”, G. K. Dixon, L. G. Copping and D. W. Holloman (Editors),BIOS Scientific Publishers, Oxford 1995, p. 175 ff.).

In particular, representatives of active compounds of the formula I (orIA and IB) having fungicidal and in part also bioregulatory activity aredescribed in the following publications:

EP-A 178 826, EP-A 203 606, EP-A 203 608, EP-A 206 523, EP-A 212 859,EP-A 226 917, EP-A 226 974, EP-A 242 070, EP-A 242 081, EP-A 243 012,EP-A 243 014, EP-A 251 082, EP-A 253 213, EP-A 254 426, EP-A 256 667,EP-A 260 794, EP-A 260 832, EP-A 267 734, EP-A 273 572, EP-A 274 825,EP-A 278 595, EP-A 280 185, EP-A 291 196, EP-A 299 694, EP-A 307 101,EP-A 307 103, EP-A 310 954, EP-A 312 221, EP-A 312 243, EP-A 329 011,EP-A 331 966, EP-A 335 519, EP-A 336 211, EP-A 337 211, EP-A 341 845,EP-A 350 691, EP-A 354 571, EP-A 363 818, EP-A 370 629, EP-A 373 775,EP-A 374 811, EP-A 378 308, EP-A 378 755, EP-A 379 098, EP-A 382 375,EP-A 383 117, EP-A 384 211, EP-A 385 224, EP-A 385 357, EP-A 386 561,EP-A 386 681, EP-A 389 901, EP-A 391 451, EP-A 393 428, EP-A 393 861,EP-A 398 692, EP-A 400 417, EP-A 402 246, EP-A 405 782, EP-A 407 873,EP-A 409 369, EP-A 414 153, EP-A 416 746, EP-A 420 091, EP-A 422 597,EP-A 426 460, EP-A 429 968, EP-A 430 471, EP-A 433 233, EP-A 433 899,EP-A 439 785, EP-A 459 285, EP-A 460 575, EP-A 463 488, EP-A 463 513,EP-A 464 381, EP-A 468 684, EP-A 468 695, EP-A 468 775, EP-A 471 261,EP-A 472 224, EP-A 472 300, EP-A 474 042, EP-A 475 158, EP-A 477 631,EP-A 480 795, EP-A 483 851, EP-A 483 985, EP-A 487 409, EP-A 493 711,EP-A 498 188, EP-A 498 396, EP-A 499 823, EP-A 503 436, EP-A 508 901,EP-A 509 857, EP-A 513 580, EP-A 515 901, EP-A 517 301, EP-A 528 245,EP-A 532 022, EP-A 532 126, EP-A 532 127, EP-A 535 980, EP-A 538 097,EP-A 544 587, EP-A 546 387, EP-A 548 650, EP-A 564 928, EP-A 566 455,EP-A 567 828, EP-A 571 326, EP-A 579 071, EP-A 579 124, EP-A 579 908,EP-A 581 095, EP-A 582 902, EP-A 582 925, EP-A 583 806, EP-A 584 625,EP-A 585 751, EP-A 590 610, EP-A 596 254, WO-A 90/07,493, WO-A92/13,830, WO-A 92/18,487, WO-A 92/18,494, WO-A 92/21,653, WO-A93/07,116, WO-A 93/08,180, WO-A 93/08,183, WO-A 93/15,046, WO-A93/16,986, WO-A 94/00,436, WO-A 94/05,626, WO-A 94/08,948, WO-A94/08,968, WO-A 94/10,159, WO-A 94/11,334, JP-A 02/121,970, JP-A04/182,461, JP-A 05/201,946, U.S. Pat. No. 5,335,283, JP-A 05/255,012,JP-A 05/294,948, JP-A 06/025,133, JP-A 06/025,142, JP-A 06/056,756, FR-A2 670 781, GB-A 2 210 041, GB-A 2 218 702, GB-A 2 238 308, GB-A 2 249092, GB-A 2 253 624, GB-A 2 255 092, WO-A 90/10006, WO-A 94/22812,EP-A-627 411, EP-A 647 631, EP-A 741 698, EP-A 738 259, EP-A 741 694,EP-A 673 923.

Suitable for the method according to the invention are generally allactive compounds of the formulae IA and IB

described in the publications mentioned at the outset in which R″ is oneof the following groups:

aryloxy with or without substitution, hetaryloxy with or withoutsubstitution, aryloxymethylene with or without substitution,hetaryloxymethylene with or without substitution, arylethenylene with orwithout substitution, and hetarylethenylene with or withoutsubstitution, or a group

R^(α)R^(β)C═NOCH₂— or R^(γ)ON═CR^(δ)CR^(ε)═NOCH₂ where the radicalsR^(α), R^(β), R^(γ), R^(δ) and R^(ε) in general and in particular havethe meanings described in the following publications:

EP-A 370 629, EP-A 414 153, EP-A 426 460, EP-A 460 575, EP-A 463 488,EP-A 472 300, EP-A 498 188, EP-A 498 396, EP-A 515 901, EP-A 585 751,WO-A 90/07,493, WO-A 92/13,830, WO-A 92/18,487, WO-A 92/18,494, WO-A93/15,046, WO-A 93/16,986, WO-A 94/08,948, WO-A 94/08,968, JP-A05/201,946, JP-A 05/255,012, JP-A 05/294,948, JP-A 06/025,133, JP-A061025,142, EP-A 738 259, EP-A 741 694, EP-A 738 259 and WO-A 95/21154,

particularly preferred radicals “aryloxy with or without substitution,hetaryloxy with or without substitution” in general and in particularhave the meanings described in the following publications:

EP-A 178 826, EP-A 242 070, EP-A 242 081, EP-A 253 213, EP-A 254 426,EP-A 256 667, EP-A 260 794, EP-A 280 185, EP-A 307 103, EP-A 341 845,EP-A 382 375, EP-A 393 861, EP-A 398 692, EP-A 405 782, EP-A 430 471,EP-A 468 684, EP-A 468 695, EP-A 477 631, EP-A 483 985, EP-A 498 188,EP-A 513 580, EP-A515 901, WO-A 93115,046, WO-A 94110,159, GB-A 2 253624 and JP-A 041182,461;

particularly preferred radicals “aryloxymethylene with or withoutsubstitution, hetaryloxymethylene with or without substitution” ingeneral and in particular have the meanings described in the followingpublications:

EP-A 178 826, EP-A 226 917, EP-A 253 213, EP-A 254 426, EP-A 278 595,EP-A 280 185, EP-A 299 694, EP-A 335 519, EP-A 350 691, EP-A 363 818,EP-A 373 775, EP-A 378 308, EP-A 385 224, EP-A 386 561, EP-A 398 692,EP-A 400 417, EP-A 407 873, EP-A 472 224, EP-A 477 631, EP-A 498 188,EP-A 498 396, EP-A 513 580, EP-A 515 901, EP-A 579 124, WO-A 93/08,180,WO-A 93/15,046, WO-A 94/00,436, JP-A 04/182,461, WO-A 90/10006, EP-A 673923 and EP-A 758 322;

particularly preferred radicals “arylethenylene, with or withoutsubstitution, hetarylethenylene with or without substitution” in generaland in particular have the meanings described in the followingpublications:

EP-A 178 826, EP-A 203 606, EP-A 253 213, EP-A 254 426, EP-A 280 185,EP-A 378 755, EP-A 398 692, EP-A 402 246, EP-A 474 042, EP-A 475 158,EP-A 477 631, EP-A 487 409, EP-A 498 188, EP-A 498 396, EP-A 513 580,EP-A 515 901, EP-A 528 245, EP-A 544 587, WO-A 93/15,046, WO-A 94/11,334and FR-A 2 670 781 and EP-A 691 332.

Particularly preferred active compounds of the formula IA in which R′ is—C[CO₂CH₃]═CHOCH₃ in general and in particular correspond to thecompounds described in the following publications:

EP-A 178 826, EP-A 203 606, EP-A 226 917, EP-A 242 070, EP-A 242 081,EP-A 256 667, EP-A 260 794, EP-A 278 595, EP-A 299 694, EP-A 307 103,EP-A 335 519, EP-A 341 845, EP-A 350 691, EP-A 370 629, EP-A 373 775,EP-A 378 308, EP-A 378 755, EP-A 382 375, EP-A 385 224, EP-A 386 561,EP-A 393 861, EP-A 402 246, EP-A 405 782, EP-A 407 873, EP-A 414 153,EP-A 426 460, EP-A 430 471, EP-A 463 488, EP-A 468 695, EP-A 472 224,EP-A 474 042, EP-A 475 158, EP-A 483 985, EP-A 487 409, EP-A 515 901,EP-A 528 245, EP-A 544 587, WO-A 90/07,493, WO-A 92118,487, WO-A92/18,494, WO-A 93/08,180, WO-A 93116,986, WO-A 94/00,436, WO-A94/08,948, WO-A 94/08,968, WO-A 94/10,159, WO-A 94111,334, FR-A 2 670781, JP-A 06/025,133, EP-A 738 259, EP-A 673 923

particularly preferred active compounds of the formula IA where R′ is—C[CO₂CH₃]═NOCH₃ in general and in particular correspond to thecompounds described in the following publications:

EP-A 253 213, EP-A 254 426, EP-A 299 694, EP-A 363 818, EP-A 378 308,EP-A 385 224, EP-A 386 561, EP-A 400 417, EP-A 407 873, EP-A 460 575,EP-A 463 488, EP-A 468 684, EP-A 472 300, EP-A 515 901, WO-A 94/00,436,WO-A 94/08,948, WO-A 94/10,159, WO-A 94/11,334, JP-A 05/201,946, JP-A05/255,012, JP-A 05/294,948, EP-A 738 259, EP-A 673 923

particularly preferred active compounds of the formula IA in which R′ is—C[CONHCH₃]═NOCH₃ in general and in particular correspond to thecompounds described in the following publications:

EP-A 398 692, EP-A 463 488, EP-A 477 631, EP-A 515 901, EP-A 579 124,EP-A 585 751, WO-A 92/13,830, WO-A 93/08,180, WO-A 94/08,948, WO-A94/10,159, WO-A 94/11,334, GB-A 2 253 624, JP-A 04/182,461, JP-A05/201,946, JP-A 05/255,012, JP-A 05/294,948, WO-A 90/10006, EP-A 741694, EP-A 673 923, EP-A 691 332 and WO-A 95/21154

particularly preferred active compounds of the formula IA in which R′ is—C[CO₂CH₃]═CHCH₃ or —C[CO₂CH₃]═CHCH₂CH₃ in general and in particularcorrespond to the compounds described in the following publications:

EP-A 280 185, EP-A 463 488, EP-A 513 580, EP-A 515 901, EP-A 738 259,EP-A 673 923 and EP-A 758 322

particularly preferred active compounds of the formula IA in which R′ is—C[COCH₃]═NOCH₃ or —C[COCH₂CH₃]═NOCH₃ in general and in particularcorrespond to the compounds described in EP-A 498 188;

particularly preferred active compounds of the formula IA in which R′ is—N(OCH₃)—CO₂CH₃, —N(CH₃)—CO₂CH₃ or —N(CH₂CH₃)—CO₂CH₃ in general and inparticular correspond to the compounds described in the followingpublications: EP-A 498 396, WO-A 93/15,046, JP-A 06/025,142 and JP-A06/056,756;

particularly preferred active compounds of the formula IB in which R is—OC[CO₂CH₃]═CHOCH₃, —OC[CO₂CH₃]═CHCH₃, —OC[CO₂CH₃]═CHCH₂CH₃,—SC[CO₂CH₃]═CHOCH₃, —SC[CO₂CH₃]═CHCH₃, —SC[CO₂CH₃]═CHCH₂CH₃,—N(CH₃)C[CO₂CH₃]═CHOCH₃, —N(CH₃)C[CO₂CH₃]═NOCH₃, —CH₂C[CO₂CH₃]═CROCH₃,—CH₂C[CO₂CH₃]═NOCH₃ or —CH₂C[CONHCH₃]═NOCH₃ in general and in particularcorrespond to the compounds described in the following publications:

EP-A 212 859, EP-A 331 966, EP-A 383 117, EP-A 384 211, EP-A 389 901,EP-A 409 369, EP-A 464 381, EP-A 471 261, EP-A 503 436, EP-A 546 387,EP-A 548 650, EP-A 579 908 and EP-A 584 625.

Examples of particularly suitable active compounds IA and IB are listedin the tables below.

TABLE 1.1A Compounds of the formula IA where Q is phenyl, R′ is—C(CO₂CH₃)═CHOCH₃, n is 0, R″ is (het)aryloxymethylene with or withoutsubstitution, where the (het)aryl group with or without substitution hasthe following meanings: No. (Het)aryl with or without substitutionLiterature I.1A-1 2-CH₃—C₆H₄ EP-A 226 917 I.1A-2 2,5-(CH₃)₂—C₆H₃ EP-A226 917 I.1A-3 2-CH₃, 4-C[CH₃]═NOCH₃—C₆H₃ EP-A 386 561 I.1A-42-CH₂CH₂CH₃, 6-CF₃-pyrimidin-4-yl EP-A 407 873

TABLE 1.1B Compounds of the formula IA where R′ is —C(CO₂CH₃)═CHOCH₃, Qis phenyl, n is 0, R″ is (het)aryloxy with or without substitution,where the (het)aryl group with or without substitution has the followingmeanings: No. (Het)aryl with or without substitution Literature I.1B-1C₆H₅ EP-A 178 826 I.1B-2 6-[2-CN—C₆H₄—O]-pyrimidin-4-yl EP-A 382 375

TABLE 1.1C Compounds of the formula IA where R′ is —C(CO₂CH₃)═CHOCH₃, Qis phenyl, n is 0, R″ is (het)arylethenylene with or without substi-tution, where the (het)aryl group with or without substitution has thefollowing meanings: No. (Het)aryl with or without substitutionLiterature I.1C-1 1-(2,4-Cl₂—C₆H₃), 5-CF₃-pyrazol-4-yl EP-A 528 245I.1C-2 1-(4-Cl—C₆H₄)-pyrazol-4-yl EP-A 378 755 I.1C-3 3-CF₃—C₆H₄ EP-A203 606 I.1C-4 3-Cl—C₆H₄ EP-A 203 606 I.1C-5 4-C₆H₅—C₆H₄ EP-A 203 606

TABLE 1.1D Compounds of the formula IA where Q is phenyl, R′ is—C(CO₂CH₃)═CHOCH₃, n is 0, R″ is CH₂ON—CR^(α)R^(β), where R^(α) andR^(β) have the following meanings: No. R^(α) R^(β) Literature I.1D-1 CH₃4-Cl—C₆H₄ EP-A 370 629 I.1D-2 CH₃ 3-CF₃—C₆H₄ EP-A 370 629 I.1D-3 CH₃4-OCH₂CH₃-pyrimidin-2-yl WO-A 92/18,487

TABLE 1.1E Compounds of the formula IA where Q is phenyl, R′ is—C(CO₂CH₃)═CHOCH₃, n is 0, R″ is CH₂ON═CR^(γ)CR^(δ)═NOR^(ε), whereR^(γ), R^(δ) and R^(ε) have the following meanings: No. R^(γ) R^(δ)R^(ε) Literature I.1E-1 CH₃ CH₃ CH₃ EP-A 738 259 I.1E-2 CH₃ CH₃ CH₂CH₃EP-A 738 259 I.1E-3 CH₃ C₆H₅ CH₃ EP-A 738 259 I.1E-4 CH₃ C₆H₅ CH₂CH₃EP-A 738 259 I.1E-5 CH₃ 4-Cl—C₆H₄ CH₃ EP-A 738 259 I.1E-6 CH₃ 4-Cl—C₆H₄CH₂CH₃ EP-A 738 259

TABLE 1.2A Compounds of the formula IA where Q is phenyl, R′ is—C(CO₂CH₃)═NOCH₃, n is 0, R″ is (het)aryloxymethylene with or withoutsubstitution, where the (het)aryl group with or without substitution hasthe following meanings: No. (Het)aryl with or without substitutionLiterature I.2A-1 2-CH₃—C₆H₄ EP-A 253 213 I.2A-2 2,5-(CH₃)₂—C₆H₃ EP-A400 417 I.2A-3 2,4-(CH₃)₂—C₆H₃ EP-A 400 417 I.2A-4 2,3,5-(CH₃)₃—C₆H₂EP-A 400 417 I.2A-5 2-Cl, 5-CH₃—C₆H₃ EP-A 400 417 I.2A-6 2-CH₃,4-C[CH₃]═NOCH₃—C₆H₃ EP-A 386 561

TABLE 1.2B Compounds of the formula IA where Q is phenyl, R′ is—C(CO₂CH₃)═NOCH₃, n is 0, R″ is (het)aryloxy with or withoutsubstitution, where the (het)aryl group with or without substitution hasthe following meanings: No. (Het)aryl with or without substitutionLiterature I.2B-1 C₆H₅ EP-A 253 213 I.2B-26-[2-CN—C₆H₄—O]-pyrimidin-4-yl EP-A 468 684

TABLE 1.2C Compounds of the formula IA where Q is phenyl, R′ is—C(CO₂CH₃)═NOCH₃, n is 0, R″ is CH₂ON—CR^(α)R^(β), where R^(α) and R^(β)have the following meanings: No. R^(α) R^(β) Literature I.2C-1 CH₃4-Cl—C₆H₄ EP-A 463 488 I.2C-2 CH₃ 3-Cl—C₆H₄ EP-A 463 488 I.2C-3 CH₃4-CF₃—C₆H₄ EP-A 463 468 I.2C-4 CH₃ 3-CF₃—C₆H₄ EP-A 463 488 I.2C-5 CH₃4-CH₃—C₆H₄ EP-A 463 488 I.2C-6 CH₃ 4-OCH₂CH₃-pyrimidin-2-yl EP-A 472 300I.2C-7 CH₃ 3,5-Cl₂—C₆H₃ EP-A 463 488

TABLE 1.2D Compounds of the formula IA where Q is phenyl, R′ is—C(CO₂CH₃)═NOCH₃, n is 0, R″ is CH₂ON═CR^(γ)CR^(δ)═NOR^(ε), where R^(γ),R^(δ) and R^(ε) have the following meanings: No. R^(γ) R^(δ) R^(ε)Literature I.2D-1 CH₃ CH₃ CH₃ EP-A 738 259 I.2D-2 CH₃ CH₃ CH₂CH₃ EP-A738 259 I.2D-3 CH₃ C₆H₅ CH₃ EP-A 736 259 I.2D-4 CH₃ C₆H₅ CH₂CH₃ EP-A 738259 I.2D-5 CH₃ 4-Cl—C₆H₄ CH₃ EP-A 736 259 I.2D-6 CH₃ 4-Cl—C₆H₄ CH₂CH₃EP-A 738 259

TABLE 1.3A Compounds of the formula IA where Q is phenyl, R′ is—C(CONHCH₃)═NOCH₃, n is 0, R″ is (het)aryloxymethylene with or withoutsubstitution, where the (het)aryl group with or without substitution hasthe following meanings: No. (Het)aryl with or without substitutionLiterature I.3A-1 2-CH₃—C₆H₄ EP-A 477 631 I.3A-2 2,5-(CH₃)₂—C₆H₃ EP-A477 631 I.3A-3 2,4-(CH₃)₂—C₆H₃ EP-A 477 631 I.3A-4 2,3,5-(CH₃)₃—C₆H₂EP-A 477 631 I.3A-5 2-CH₃, 4-C[CH₃]═NOCH₃—C₆H₃ EP-A 579 124 I.3A-61-[4-Cl—C₆H₄]-pyrazol-3-yl WO-A 90/10006 I.3A-71-[2,4-Cl₂—C₆H₃]-pyrazol-3-y1 WO-A 90/10006

TABLE 1.3B Compounds of the formula IA where Q is phenyl, R′ is—C(CONHCH₃)═NOCH₃, n is 0, R″ is (het)aryloxy with or withoutsubstitution, where the (het)aryl group with or without substitution hasthe following meanings: No. (Het)aryl with or without substitutionLiterature I.3B-1 C₆H₅ EP-A 398 692 I.3B-26-[2-CN—C₆H₄—O]-pyrimidin-4-yl GB-A 2 253 624

TABLE 1.3C Compounds of the formula IA where Q is phenyl, R′ is—C(CONHCH₃) = NOCH₃, n is 0, R″ is (het)arylethenylene with or withoutsubstitution, where the (het)aryl group with or without substitution hasthe following meaning: (Het)aryl with or without sub- No. stitutionLiterature I.3C-1 1-[2,4-Cl₂—C₆H₃], EP-A 691 332 5-CF₃-pyrazol-4-yl

TABLE 1.3D Compounds of the formula IA where Q is phenyl, R′ is—C(CONHCH₃)═NOCH₃, n is 0, R″ is CH₂ON═CR^(α)R^(β), where R^(α) andR^(β) have the following meanings: No. R^(α) R^(β) Literature I.3D-1 CH₃4-Cl—C₆H₄ EP-A 463 488 I.3D-2 CH₃ 3-Cl—C₆H₄ EP-A 463 488 I.3D-3 CH₃4-CF₃—C₆H₄ EP-A 585 751 I.3D-4 CH₃ 3-CF₃—C₆H₄ EP-A 585 751 I.3D-5 CH₃4-CH₃—C₆H₄ EP-A 463 488 I.3D-6 CH₃ 3,5-Cl₂—C₆H₃ EP-A 463 488 I.3D-7 CH₃2-OCH₂CH₃—pyrimidin-2-yl WO-A 92/13,830

TABLE 1.3E Compounds of the formula IA where Q is phenyl, R′ is—C(CONHCH₃)═NOCH₃, n is 0, R″ is CH₂ON═CR^(γ)CR^(δ)═NOR^(ε), whereR^(γ), R^(δ) and R^(ε) have the following meanings: No. R^(γ) R^(δ)R^(ε) Literature I.3E-1 CH₃ CH₃ CH₃ WO-A 95/21154 I.3E-2 CH₃ CH₃ CH₂CH₃WO-A 95/21154 I.3E-3 CH₃ C₆H₅ CH₃ WO-A 95/21154 I.3E-4 CH₃ C₆H₅ CH₂CH₃WO-A 95/21154 I.3E-5 CH₃ 4-Cl—C₆H₄ CH₃ WO-A 95/21154 I.3E-6 CH₃4-Cl—C₆H₄ CH₂CH₃ WO-A 95/21154

TABLE 1.4A Compounds of the formula IA where Q is phenyl, R′ is—C(CO₂CH₃)═CHCH₃, n is 0, R″ is (het)aryloxymethylene with or withoutsubstitution when the het(aryl) group with or without substitution hasthe following meanings: (Het)aryl with or without sub- No. stitutionLiterature I.4A-1 2-CH₃—C₆H₄ EP-A 280 185 I.4A-2 2,5-(CH₃)₂—C₆H₃ EP-A513 580 I.4A-3 2,4-(CH₃)₂—C₆H₃ EP-A 513 580 I.4A-4 2,3,5-(CH₃)₃—C₆H₂EP-A 513 580 I.4A-5 2-Cl, 5-CH₃—C₆H₃ EP-A 513 580 I.4A-6 2-CH₃,4-C[CH₃]═NOCH₃—C₆H₃ EP-A 513 580 I.4A-7 1-[4-Cl—C₆H₄]-pyrazol-3-yl EP-A758 322

TABLE 1.4B Compounds of the formula IA where Q is phenyl, R′ is—C(CO₂CH₃) = CHCH₃, n is 0, R″ is (het)aryloxy with or without sub-stitution, where the (het)aryl group with or without substitution hasthe following meaning: (Het)aryl with or without sub- No. stitutionLiterature I.4B-1 C₆H₅ EP-A 513 580

TABLE 1.4C Compounds of the formula IA where Q is phenyl, R′ is—C(CO₂CH₃) = CHCH₃, n is 0, R″ is CH₂ON = CR^(γ)CR^(δ) = NOR^(ε), whereR^(γ), R^(δ) and R^(ε) have the following meanings: No. R^(γ) R^(δ)R^(ε) Literature I.4C-1 CH₃ CH₃ CH₃ EP-A 738 259 I.4C-2 CH₃ CH₃ CH₂CH₃EP-A 738 259 I.4C-3 CH₃ C₆H₅ CH₃ EP-A 738 259 I.4C-4 CH₃ C₆H₅ CH₂CH₃EP-A 738 259 I.4C-5 CH₃ 4-Cl—C₆H₄ CH₃ EP-A 738 259 I.4C-6 CH₃ 4-Cl—C₆H₄CH₂CH₃ EP-A 73B 259

TABLE 1.5A Compounds of the formula IA where Q is phenyl, R′ is—C(CO₂CH₃)═CHCH₂CH₃, n is 0, R″ is (het)aryloxymethylene with or withoutsubstitution, where the (het)aryl group with or without substitution hasthe following meanings: (Het)aryl with or without No. substitutionLiterature I.5A-1 2-CH₃—C₆H₄ EP-A 513 580 I.5A-2 2,5-(CH₃)₂—C₆H₃ EP-A513 580 I.5A-3 2,4-(CH₃)₂—C₆H₃ EP-A 513 580 I.5A-4 2,3,5-(CH₃)₃—C₆H₂EP-A 513 580 I.5A-5 2-Cl, 5-CH₃—C₆H₃ EP-A 513 580 I.5A-6 2-CH₃,4-C[CH₃]═NOCH₃—C₆H₃ EP-A 513 580

TABLE 1.5B Compounds of the formula IA where Q is phenyl, R′ is—C(CO₂CH₃) = CHCH₂CH₃, n is 0, R″ is (het)aryloxy with or withoutsubstitution, where the (het)aryl group with or without substitu- tionhas the following meaning: (Het)aryl with or without sub- No. stitutionLiterature I.5B-1 C₆H₅ EP-A 513 580

TABLE 1.5C Compounds of the formula IA where Q is phenyl, R′ is—C(CO₂CH₃) = CHCH₂CH₃, n is 0, R″ is CH₂ON = CR^(γ) CR^(δ)= NOR^(ε) ,where R^(γ), R^(δ) and R^(ε) have the following meanings: No. R^(γ)R^(δ) R^(ε) Literature I.5C-1 CH₃ CH₃ CH₃ EP-A 738 259 I.5C-2 CH₃ CH₃CH₂CH₃ EP-A 738 259 I.5C-3 CH₃ C₆H₅ CH₃ EP-A 738 259 I.5C-4 CH₃ C₆H₅CH₂CH₃ EP-A 738 259 I.5C-5 CH₃ 4-Cl—C₆H₄ CH₃ EP-A 738 259 I.5C-6 CH₃4-Cl—C₆H₄ CH₂CH₃ EP-A 738 259

TABLE 1.6A Compounds of the formula IA where Q is phenyl, R′ is—C(COCH₃)═NOCH₃, n is 0, R″ is (het)aryloxymethylene with or withoutsubstitution, where the (het)aryl group with or without substitution hasthe following meanings: (Het)aryl with or without No. substitutionLiterature I.6A-1 2-CH₃—C₆H₄ EP-A 498 188 I.6A-2 2,5-(CH₃)₂—C₆H₃ EP-A498 188 I.6A-3 2,4-(CH₃)₂—C₆H₃ EP-A 498 188 I.6A-4 2,3,5-(CH₃)₃—C₆H₂EP-A 498 188 I.6A-5 2-CH₃, 4-C[CH₃]═NOCH₃—C₆H₃ EP-A 498 188

TABLE 1.6B Compounds of the formula IA where Q is phenyl, R′ is—C(COCH₃)═NOCH₃, n is 0, R″ is (het)aryloxy with or without sub-stitution, where the (het)aryl group with or without substitution hasthe following meanings: (Het)aryl with or without No. substitutionLiterature I.6B-1 C₆H₅ EP-A 498 188 I.6B-26-[2-CN—C₆H₄—O]-pyrimidin-4-yl EP-A 498 188

TABLE 1.7A Compounds of the formula IA where Q is phenyl, R′ is—C(COCH₂CH₃)═NOCH₃, n is 0, R″ is (het)aryloxymethylene with or withoutsubstitution, where the (het)aryl group with or without substitution hasthe following meanings: (Het)aryl with or without No. substitutionLiterature I.7A-1 2-CH₃—C₆H₄ EP-A 498 188 I.7A-2 2,5-(CH₃)₂—C₆H₃ EP-A498 188 I.7A-3 2,4-(CH₃)₂—C₆H₃ EP-A 498 188 I.7A-4 2,3,5-(CH₃)₃—C₆H₂EP-A 498 188 I.7A-5 2-CH₃, 4-Cl[CH₃]═NOCH₃—C₆H₃ EP-A 498 188

TABLE 1.7B Compounds of the formula IA where Q is phenyl, R′ is—C(COCH₂CH₃)═NOCH₃, n is 0, R″ is (het)aryloxy with or withoutsubstitution, where the (het)aryl group with or without substitu- tionhas the following meanings: No. (Het)aryl with or without substitutionLiterature I.7B-1 C₆H₅ EP-A 498 188 I.7B-26-[2-CN—C₆H₄—O]-pyrimidin-4-yl EP-A 498 188

TABLE 1.8A Compounds of the formula IA where Q is phenyl, R′ is—N(OCH₃)—CO₂CH₃, n is 0, R″ is (het)aryloxymethylene with or withoutsubstitution, where the (het)aryl group with or without substitution hasthe following meanings: No. (Het)aryl with or without substitutionLiterature I.8A-1 2-CH₃—C₆H₄ WO-A 93/15,046 I.8A-2 2,5-(CH₃)₂—C₆H₃ WO-A93/15,046 I.8A-3 2,4-(CH₃)₂—C₆H₃ WO-A 93/15,046 I.8A-4 2,3,5-(CH₃)₃—C₆H₂WO-A 93/15,046 I.8A-5 2-Cl, 5-CH₃—C₆H₃ WO-A 93/15,046 I.8A-6 2-CH₃,4-C[CH₃]═NOCH₃—C₆H₃ WO-A 93/15,046 I.8A-7 2-CH₃, 4-C[CH₃]═NOCH₂CH₃—C₆H₃WO-A 93/15,046 I.8A-8 2-CH₃, 4-C[CH₂CH₃]═NOCH₃—C₆H₃ WO-A 93/15,046I.8A-9 2-CH₃, 4-C[CH₂CH₃]═NOCH₂CH₃—C₆H₃ WO-A 93/15,046 I.8A-101-[4-Cl—C₆H₄]-pyrazol-3-yl WO-A 96/01256 

TABLE 1.8B Compounds of the formula IA where Q is phenyl, R′ is—N(OCH₃)—CO₂CH₃, n is 0, R″ is CH₂ON = CR^(α)R^(β), where R^(α) andR^(β) have the following meaning: No. R^(α) R^(β) Literature I.8B-1 CH₃3,5-Cl₂—C₆H₃ WO-A 93/15,046

It can be assumed that the method according to the invention can beemployed in principle in all crop plants and horticulturally usefulplants having a modified pathogen resistance against harmful fungi.Examples of such plants are bananas, coffee, potatoes, rape seed,turnips, asparagus, tea, tomatoes, onion species, and gramineae such asbarley, oats, maize, rice, rye and wheat; the effect is particularlypronounced in potatoes, turnips, asparagus, onion species and gramineae,and the method according to the invention is particularly recommendedfor use in gramineae, for example in wheat, barley and rice. Methods forincreasing the pathogen resistance of such crop plants are well known toa person skilled in the art and described in the literature, for examplein WO-A 95/05467, WO-A 94/8009 and the publications J. Lamb et al.,Biotechnology 10 (1992), 1436-1445, H. Anzai et al., Mol. Gen. Genet.219 (1989), 492-494, R. Grison et al., Nature Biotechnology 14 (1996),643-646, H. Uchimiya et al., Biotechnology 11 (1993), 835-837, G. Jachet al., Biopractice 1 (1992), 33-40, J. Logemann et al, Biotechnology 10(1992), 305-308 and G. Strittmatter et al., Biotechnology 13 (1995),1085-1089.

Depending on the kind of crop plant, the application rates of compoundsIA or IB are from 0.5 to 0.01 kg/ha, preferably 0.3 to 0.01 kg/ha, inparticular 0.15 to 0.05 kg/ha.

For the method according to the invention, the compounds I can beformulated and applied in a manner customary for use in crop protection(cf. literature cited at the outset).

The method according to the invention has the advantage, among others,that a large number of harmful fungi can be controlled successfully withjust one active compound of the formula I; according to the prior art,this would have required a plurality of fungicidally active compoundswhich may in certain cases have had adverse interactions.

In some instances, the application rates of the active compounds of theformula I could be considerably reduced as compared to the customaryapplication rates, without adversely affecting the activity. This resultis surprising. In the case of kresoxim-methyl (methylmethoxyimino-α-(o-tolyloxy)-o-tolylacetate), for example, applicationrates of below 0.05 kg/ha, in particular from 0.04 to 0.01 kg/ha, aresufficient.

The method according to the invention can be employed particularlyadvantageously in crop plants which have an increased pathogenresistance to those harmful fungi which in general cannot be controlledcompletely with the individual active compounds of the formula I. Thus,it is possible to improve the usually insufficient activity ofazoxystrobin(methyl(E)-2-(2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl)-3-methoxyacrylate)against cereal mildew in mildew-resistant barley or wheat varietiesdisproportionally.

The method according to the invention can also be employed successfullyin crop plants having an increased pathogen resistance to those harmfulfungi which can be effectively controlled with active compounds of theformula I. Here, it is often possible to reduce the required applicationrate considerably.

For example, less of the active compound kresoxim-methyl is required torender entirely free of infection those varieties of crop plants such aswheat, barley, grapevines or apple trees which have increased resistanceto powdery mildew species, compared to the higher application rates ofactive strobilurin ingredient which are required to render nonresistantplants mildew-free. Comparative experiments show clearly that in thebarley varieties A HOR 1528/9, A HOR 2978/80, A HOR 3141/78 and A HOR 155458/70, which have increased mildew resistance, considerably loweramounts of kresoxim-methyl allow the same control of barley mildew as inthe common, commercially available varieties “Asse” and “Sonja” which donot have any increased mildew resistance.

The same applies to resistant and nonresistant grapevines and theirtreatment with kresoxim-methyl for controlling Plasmopara viticola.

This applies correspondingly to the active compound azoxystrobin for thecontrol of a large number of different phytopathogenic fungi inresistant and nonresistant crop plants. Examples of economicallyimportant phytopathogenic fungi include the following pathogen/hostpairs from the class of the idiomcetes: Puccinia species in cereals andlawns, Rhizoctonia species in cotton, rice and lawns, Hemileia vastatrixin coffee, Ustilago species in cereals and sugar cane; from the group ofthe Ascomycetes Erysiphe species in wheat, barley and rye, Erysiphe andSphaerotheca species in curcurbits, Podosphaera leucotricha in apples,Uncinula necator in grapevines, Venturia species in apples and pears;from the class of the Deuteromycetes Botrytis cinerea in strawberries,grapevines, vegetables and ornamentals, Alternaria species in vegetablesand fruit, Pyricularia oryzae in rice and lawns, Cercospora arachidicolain groundnuts, Pseudocercosporella herpotichoides in wheat and barley,Helminthosporium species in cereals, Septoria species in cereals andvegetables; and from the class of the Phycomycetes Phytophthorainfestans in tomatoes and potatoes, Plasmopara viticola in grapevinesand Pseudoperonospora species in hops and vegetables.

COMPARATIVE EXPERIMENT

Activity against powdery mildew of barley (Exysiphe graminis f. sp.hordei)

Leaves of potted barley seedlings of the various varieties were sprayedto runoff point with an aqueous active compound formulation preparedfrom a stock solution comprising 10% of active compound(kresoxim-methyl), 63% of cyclohexanone and 27% of emusifier. The nextday, the leaves were dusted with spores of powdery mildew of barley(Erysiphe graminis f. sp. hordei). The test plants were subsequentlykept in a greenhouse at 20°-22° C. and 75-80% relative atmospherichumidity. 6 days after the inoculation, the extent of mildew developmentwas determined visually as % infection of the total leaf area treated.

Barley variety % infection of the leaves after application of aqueouskresoxim-methyl formulation, kresoxim-methyl content in ppm

2 1 0.5 0.25 ppm ppm ppm ppm Untreated “Asse” 7 80 100 100 100commercially available vari- ety “Sonja” 5 70 100 100 100 commerciallyavailable vari- ety

Varieties having increased resistance to mildew

A HOR 1528/91 0 7 30 90 100 A HOR 2978/80 2 15 40 90 100 A HOR 3141/78 110 70 100 100 A HOR 5458/70 0 2 40 90 100

The barley seedlings (Hordeum vulgaris) of the varieties used in thecomparative experiment can be obtained from: Institut fürPflanzengenetik und Kulturpflanzenforschung Gatersleben, Genbank,Corrensstr. 3, 06466 Gatersleben, Germany.

We claim:
 1. A method for controlling harmful fungi in crop plants,wherein the crop plants have a moitied pathogen resistance to saidharmful fungi and wherein said harmful fungi belong to a class selectedfrom the group consisting of Basidiomycetes, Ascomycetes, Deuteromycetesand Phycomycetes, which comprises treating the plants with an effectiveamount of active compound of formula IA or IB

where ... is a single or double bond and where: R′ is —C[CO₂CH₃]═CHOCH₃,—C[CO₂CH₃]═NOCH₃, —C[CONHCH₃]═NOCH₃, —[CO₂CH₃]═CHCH₃,—C[CO₂CH₃]═CHCH₂CH₃, —C[COCH₃)═NOCH₃, —C[COCH₂CH₃]═NOCB₃,—N(OCH₃)—CO₂CH₃, —N(CH₃)—CO₂CH₃, —N(CH₂CH₃)—CO₂CH₃, R″ is a C-organicradical which is attached directly or via an oxy, mercapto, amino oralkylamino group, or together with a group X and the ring Q or T towhich they are attached forms a bicyclic, partially or fully unsaturatedsystem with or without substitution which may, in addition to carbonring members, contain hetero atoms from the group consisting of oxygen,sulfur and nitrogen, R^(x) is —OC[CO₂CH₃]═CHOCH₃, —OC[CO₂CH₃]═CHCH₃,—OC[ CO₂CH₃]═CHCH₂CH₃, —SC[CO₂CH₃]═CHOCH₃, —SC[CO₂CH₃]═CHCH₃,—SC[CO₂CH₃]═CHCH₂CH₃, —N(CH₃)C [CO₂CH₃]═CHOCH₃, —N(CH₃)C[CO₂CH₃]═NOCH₃,—CH₂C[CO₂CH₃]═CHOCH₃, —CH₂C[CO₂CH₃]═NOCH₃, —CH₂C[CONCH₃]═NOCH₃, R^(y) isoxygen, sulfur, ═CH— or ═N—, n is 0, 1, 2 or 3, where the radicals X maybe different if n>1; X is cyano, nitro, halogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkozy, C₁-C₄-alkylthio or, ifn>1a C₃-C₅-alkylene, C₃-C₅-alkenylene, oxy-C₂-C₄-alkylene,oxy-C₁-C₃-alkylenoxy, oxy-C₂-C₄-alkenylene, oxy-C₂-C₄-alkenylenoxy orbutadienediyl group which is attached to two adjacent carbon atoms ofthe phenyl ring, where these chains in turn may carry one to three ofthe following radicals: halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy, C₁-C₄-haloalkozy or C₁-C₄-alkylthio, Y is ═C— or —N—, Q isphenyl, pyrrolyl, thienyl, furyl, pyrazolyl, inidazolyl, oxazolyl,isoxazolyl, thiazolyl, thiadiazolyl, triazolyl, pyridinyl, 2-pyridonyl,pyrimidinyl and triazinyl, T is phenyl, oxazolyl, thiazolyl,thiadiazolyl, oxadiazolyl, pyridinyl, pyrimidinyl and triazinyl.
 2. Amethod as claimed in claim 1, wherein the crop plants are treated withfrom 0.5 to 0.01 kg/ha of a compound of the formula IA or IB.
 3. Themethod of claim 1 wherein the the active compound is of formula IAwherein Q denotes phenyl and wherein R′ is —C(CO₂CH₃)═CHOCH₃, and R″ isselected from the group consisting of 2-methylphenoxyme-thylene,2,5-dimethylphenoxymethylene,2-methyl-4-(1-methoxyimino)ethylphenoxymethylene,2-propyl-6-trifluoromethylpyrimidin-4-yloxymethylene,2,4-dimethylphenoxymethylene, phenoxy,6-(2-cyanophenoxy)pyrimidin-4-yloxy,2-(1-(2,4-dichlorophenyl)-5-trifluoromethylpyrazol-4-yl)ethylene,2-(1-(4-chlorophenyl)pyrazol-4-yl)ethylene,2-(2-trifluoromethylphenyl)ethylene, 2-(3-chlorophenyl)ethylene,2-(4-biphenyl)ethylene, a group CH₂ON═C(CH₃)R^(β) and a groupCH₂ON═C(CH₃)CR^(δ)═NOR^(ε), wherein R^(β) is 4-chlorophenyl,3-trifluoromethylphenyl or 4-ethoxypyrimidin-2-yl; R^(δ) is methyl,phenyl or 4-chlorophenyl; and R^(ε) is methyl or ethyl; or R′ is—C(CO₂CH₃)═NOCH₃, and R″ is selected from the group consisting of2-methylphenoxymethylene, 2,5-dimethylphenoxymethylene,2,4-dimethylphenoxymethylene, 2,3,5-trimethylphenoxymethylene,2-chloro-5-methylphenoxymethylene,2-methyl-4-(1-methoxyimino)ethylphenoxymethylene, phenoxy,6-(2-cyanophenoxy)pyrimidin-4-yloxy, a group CH₂ON═C(CH₃)R^(β) and agroup CH₂ON═C(CH₃)CR^(δ)═NOR^(ε), wherein R^(β) is 4-chlorophenyl,3-chlorophanyl, 4-trifluoromethylphenyl, 3-trifluoromethylphenyl,4-ethoxypyrimidin-2-yl or 3,5-dichlorophenyl; R^(δ) is methyl, phenyl or4-chlorophenyl; and R^(ε) is methyl or ethyl; or R′ is—C(CONHCH₃)═NOCH₃, and R″ is selected from the group consisting of2-methylphenoxymethylene, 2,5-dimethylphenoxymethylene,2,4-dimethylphenoxymethylene, 2,3,5-trimethylphenozymethylene,2-methyl-4-(1-methoxyimino)ethylphenoxymethylene,1-(4-chlorophenyl)pyrazol-3-yloxymethylene,1-(2,4-dichlorophenyl)pyrazol-3-yloxymethylene, phenoxy,6-(2-cyanophenoxy)pyrimidin-4-yloxy, a group CH₂ON═C(CH₃)R^(β) and agroup CH₂ON═C(CH₃)CR^(δ)═NOR^(ε), wherein R^(β) is 4-chlorophenyl,3-chlorophenyl, 4-trifluoromethylphenyl, 3-trifluoromethylphenyl,3,5-dichlorophenyl or 4-ethoxypyrimidin-2-yl; R^(δ) is methyl, phenyl or4-chlorophenyl; and R^(ε) is methyl or ethyl; or R^(δ) is 4-fluorophenyland R^(ε) is mothyl; or R′ is —C(CO₂CH₃)═CHCH₃, and R″ is selected rromthe group consisting of 2-methylphenoxymethylene,2,5-dimethylphenoxymethylene, 2,4-dimethylphenoxymethylene,2,3,5-trimethylphenoxymethylene, 2-chloro-5-methylphenoxymethylene,2-methyl-4-(1-methoxyimino)ethylphenoxymethylene,1-(4-chlorophenyl)pyrazol-3-yloxymethylene, phenoxy and a groupCH₂ON═C(CH₃)CR^(δ)═NOR^(ε), wherein R^(δ) is methyl, phenyl or4-chlorophenyl; and R^(ε) is methyl or ethyl; or R′ is—C(CO₂CH₃)═CHCH₂CH₃, and R″ is selected from the group consisting of2-methylphenoxymethylene, 2,5-dimethylphenoxymethylene,2,4-dibmethylhenoxymethylene, 2,3,5-trimethylphanoxymethylens,2-chloro-5-methylphanoxymethylene,2-methyl-4-(1-methoxyimino)ethylphenoxymethylene, phenoxy and a groupCH₂ON═C(CH₃)CR^(δ)═NOR^(ε), wherein R^(δ) is methyl, phenyl or4-chlorophenyl; and R^(ε) is methyl or ethyl; or R′ is —C(COCH₃)═NOCH₃or —C(COCH₂CH₃)═NOCH₃, and R″ is selected from the group consisting of2-methylphenoxymethylene, 2,5-dimethylphethylene,2,4-dimethylphenoxymethylene, 2,3,5-trimethylphenozymethylene,2-methyl-4-(1-methoxyimino)ethylphenoxymethylene, phenoxy and6-(2-cyanophenoxy)pyrimidin-4-yloxy, or R′ is —N(OCH₃)—CO₂CH₃, and R″ isselected from the group consisting of 2-methylphenoxymethyleno,2,5-dimethylphenoxymethylene, 2,4-dimethylhenoxymethylene,2,3,5-trimethylphenoxymethylene, 2-chloro-5-methylphenoxymethylene,2-methyl-4-(1-methoxyimino)ethylphenoxymethylene,2-methyl-4-(1-methoxyimino)propylphenoxymethylene,2-methyl-4-(1-methoxyimino)propylphenoxymethylene,1-(4-chlorophenyl)pyrazol-3-yloxymethyl andCH₂ON═C(CH₃)(3,5-dichlorophenyl).
 4. The method of claim 1 wherein theactive compound is selected from the group consisting of compoundsI.1B-2, I.2A-1, I.2C-4, I.3A-2, I.3B-1 and I.8A-10, having the followingformulae:


5. The method of claim 1 wherein the crop plants have an increasedpathogen resistance to harmful fungi.
 6. The method of claim 5 whereinthe crop plants are selected from the group consisting of bananas,coffee, potatoes, rape seed, turnips, asparagus, tea, tomatoes, onionspecies and granineae.
 7. The method of claim 5 wherein the crop plantsare selected from the group consisting of barley, oats, maize, rice, ryeand wheat.
 8. The method of claim 5 wherein the crop plants are selectedfrom the group consisting of barley, rice and wheat.
 9. The method ofclaim 5 wherein the active compound is methylmethoxyimino-α-(o-tolyloxy)-o-tolylacetate.
 10. The method of claim 9wherein the active compound is applied in an amount of less than 0.05kg/ha.
 11. The method of claim 10 wherein the active compound is appliedin an amount of from 0.04 to 0.01 kg/ha.
 12. The method of claim 9,wherein the crop plants are grapevines.
 13. The method of claim 12,wherein the pathogen is Plasmopara viticola.
 14. The method of claim 5wherein the active compound is methyl(E)-2-{2-[6-(2-cyanophenozy)pyrimidin-4-yloxyl]phenyl}-3-methoxyacrylate.15. The method of claim 14 wherein the pathogen is cereal mildew. 16.The method of claim 14 wherein the crop plant is mildew-resistant barleyor wheat.
 17. The method of claim 1, wherein the harmful fungi areselected from the group consisting of Puccinia species, Rhizoctoniaspecies, Hemilaia vastatrix, Ustilago species, Erysiphe species,Sphaerotheca species, Podosphaera leucotricha, Uncinula necator,Venturia species, Botrytis cinerea, Alternaria species, Pyriculariaoryzae, Cercospora arachidicola, Pseudocercosporella herpotichoides,Helminthosporium species, Septoria species, Phytophthora infestans,Plasmopara viticola and Pseudoperonospora species.